The title compound, C13H30N3+·Cl-, is a phase-transfer catalyst. The geometry at the central C atom of the guanidinium cation, which lies on a twofold rotation axis, is almost ideal trigonal planar, with N-C-N angles of 119.8 (2) and 120.08 (11)°. The chloride anion also lies on a twofold rotation axis.
Supporting information
CCDC reference: 618967
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.139
- Data-to-parameter ratio = 19.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97.
Hexaethylguanidinium chloride
top
Crystal data top
C13H30N3+·Cl− | F(000) = 584 |
Mr = 262.86 | Dx = 1.077 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 7.3110 (15) Å | θ = 10–14° |
b = 16.274 (3) Å | µ = 0.22 mm−1 |
c = 13.802 (3) Å | T = 293 K |
β = 97.77 (3)° | Block, white |
V = 1627.1 (6) Å3 | 0.40 × 0.20 × 0.20 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 1191 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.013 |
Graphite monochromator | θmax = 26.0°, θmin = 2.5° |
ω/2θ scans | h = 0→8 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→20 |
Tmin = 0.916, Tmax = 0.957 | l = −16→16 |
1710 measured reflections | 3 standard reflections every 200 reflections |
1582 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.139 | w = 1/[σ2(Fo2) + (0.07P)2 + 0.96P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
1582 reflections | Δρmax = 0.28 e Å−3 |
80 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.018 (2) |
Special details top
Experimental. Spectroscopic analysis, 1H NMR (CDCl3, δ, p.p.m.): 1.5 (t, 3H), 1.4 (t,
1H), 2.9 (q, 1H), 3.2 (m, 1 H), 3.6 (m, 1H). |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl | 0.0000 | 0.29804 (7) | 0.7500 | 0.0777 (4) | |
N1 | 0.5000 | 0.21906 (13) | 0.7500 | 0.0360 (5) | |
N2 | 0.4707 (2) | 0.34241 (9) | 0.66536 (11) | 0.0353 (4) | |
C1 | 0.5000 | 0.30115 (15) | 0.7500 | 0.0310 (6) | |
C2 | 0.6623 (4) | 0.37726 (17) | 0.5362 (2) | 0.0705 (8) | |
H2A | 0.7090 | 0.3552 | 0.4799 | 0.106* | |
H2B | 0.7637 | 0.3928 | 0.5844 | 0.106* | |
H2C | 0.5875 | 0.4246 | 0.5175 | 0.106* | |
C3 | 0.2620 (3) | 0.11004 (15) | 0.7258 (2) | 0.0676 (7) | |
H3A | 0.1818 | 0.0813 | 0.6763 | 0.101* | |
H3B | 0.1895 | 0.1372 | 0.7692 | 0.101* | |
H3C | 0.3442 | 0.0716 | 0.7621 | 0.101* | |
C4 | 0.2071 (3) | 0.41784 (16) | 0.57329 (17) | 0.0570 (6) | |
H4A | 0.1411 | 0.4689 | 0.5715 | 0.085* | |
H4B | 0.1243 | 0.3734 | 0.5816 | 0.085* | |
H4C | 0.2574 | 0.4107 | 0.5131 | 0.085* | |
C5 | 0.5470 (3) | 0.31281 (13) | 0.57880 (15) | 0.0486 (6) | |
H5A | 0.4464 | 0.2964 | 0.5294 | 0.058* | |
H5B | 0.6226 | 0.2647 | 0.5964 | 0.058* | |
C6 | 0.3727 (3) | 0.17285 (13) | 0.67829 (16) | 0.0468 (5) | |
H6A | 0.4430 | 0.1452 | 0.6332 | 0.056* | |
H6B | 0.2889 | 0.2110 | 0.6409 | 0.056* | |
C7 | 0.3624 (3) | 0.41870 (12) | 0.65798 (14) | 0.0413 (5) | |
H7A | 0.4437 | 0.4646 | 0.6500 | 0.050* | |
H7B | 0.3108 | 0.4270 | 0.7184 | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl | 0.0511 (5) | 0.0848 (7) | 0.1008 (8) | 0.000 | 0.0235 (5) | 0.000 |
N1 | 0.0369 (12) | 0.0322 (11) | 0.0381 (12) | 0.000 | 0.0022 (9) | 0.000 |
N2 | 0.0362 (8) | 0.0346 (8) | 0.0350 (8) | 0.0016 (6) | 0.0043 (6) | 0.0021 (7) |
C1 | 0.0225 (11) | 0.0326 (13) | 0.0376 (14) | 0.000 | 0.0037 (10) | 0.000 |
C2 | 0.0666 (16) | 0.0807 (18) | 0.0701 (17) | 0.0052 (14) | 0.0311 (14) | 0.0197 (14) |
C3 | 0.0617 (15) | 0.0540 (14) | 0.0862 (19) | −0.0210 (12) | 0.0070 (13) | 0.0011 (13) |
C4 | 0.0445 (12) | 0.0632 (15) | 0.0588 (14) | 0.0041 (10) | −0.0090 (10) | 0.0093 (11) |
C5 | 0.0574 (13) | 0.0510 (12) | 0.0395 (11) | 0.0046 (10) | 0.0140 (9) | 0.0023 (9) |
C6 | 0.0500 (12) | 0.0391 (11) | 0.0499 (12) | −0.0072 (9) | 0.0016 (9) | −0.0057 (9) |
C7 | 0.0393 (11) | 0.0362 (10) | 0.0465 (11) | 0.0036 (8) | −0.0015 (8) | 0.0045 (8) |
Geometric parameters (Å, º) top
N1—C1 | 1.336 (3) | C3—H3B | 0.9600 |
N1—C6 | 1.470 (2) | C3—H3C | 0.9600 |
N2—C1 | 1.3393 (19) | C4—C7 | 1.516 (3) |
N2—C5 | 1.467 (2) | C4—H4A | 0.9600 |
N2—C7 | 1.469 (2) | C4—H4B | 0.9600 |
C1—N2i | 1.3393 (19) | C4—H4C | 0.9600 |
C2—C5 | 1.514 (3) | C5—H5A | 0.9700 |
C2—H2A | 0.9600 | C5—H5B | 0.9700 |
C2—H2B | 0.9600 | C6—H6A | 0.9700 |
C2—H2C | 0.9600 | C6—H6B | 0.9700 |
C3—C6 | 1.507 (3) | C7—H7A | 0.9700 |
C3—H3A | 0.9600 | C7—H7B | 0.9700 |
| | | |
C1—N1—C6 | 120.76 (11) | H4A—C4—H4B | 109.5 |
C6—N1—C6i | 118.5 (2) | C7—C4—H4C | 109.5 |
C1—N2—C5 | 120.81 (15) | H4A—C4—H4C | 109.5 |
C1—N2—C7 | 120.37 (15) | H4B—C4—H4C | 109.5 |
C5—N2—C7 | 118.82 (15) | N2—C5—C2 | 112.45 (18) |
N1—C1—N2i | 120.09 (11) | N2—C5—H5A | 109.1 |
N1—C1—N2 | 120.08 (11) | C2—C5—H5A | 109.1 |
N2i—C1—N2 | 119.8 (2) | N2—C5—H5B | 109.1 |
C5—C2—H2A | 109.5 | C2—C5—H5B | 109.1 |
C5—C2—H2B | 109.5 | H5A—C5—H5B | 107.8 |
H2A—C2—H2B | 109.5 | N1—C6—C3 | 112.48 (17) |
C5—C2—H2C | 109.5 | N1—C6—H6A | 109.1 |
H2A—C2—H2C | 109.5 | C3—C6—H6A | 109.1 |
H2B—C2—H2C | 109.5 | N1—C6—H6B | 109.1 |
C6—C3—H3A | 109.5 | C3—C6—H6B | 109.1 |
C6—C3—H3B | 109.5 | H6A—C6—H6B | 107.8 |
H3A—C3—H3B | 109.5 | N2—C7—C4 | 112.72 (17) |
C6—C3—H3C | 109.5 | N2—C7—H7A | 109.0 |
H3A—C3—H3C | 109.5 | C4—C7—H7A | 109.0 |
H3B—C3—H3C | 109.5 | N2—C7—H7B | 109.0 |
C7—C4—H4A | 109.5 | C4—C7—H7B | 109.0 |
C7—C4—H4B | 109.5 | H7A—C7—H7B | 107.8 |
| | | |
C6—N1—C1—N2i | 143.71 (13) | C1—N2—C5—C2 | −125.3 (2) |
C6i—N1—C1—N2i | −36.29 (13) | C7—N2—C5—C2 | 54.2 (3) |
C6—N1—C1—N2 | −36.29 (13) | C1—N1—C6—C3 | −127.42 (15) |
C5—N2—C1—N1 | −38.05 (18) | C6i—N1—C6—C3 | 52.58 (15) |
C7—N2—C1—N1 | 142.47 (12) | C1—N2—C7—C4 | −127.80 (18) |
C5—N2—C1—N2i | 141.95 (18) | C5—N2—C7—C4 | 52.7 (2) |
C7—N2—C1—N2i | −37.53 (12) | | |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5B···N1 | 0.97 | 2.52 | 2.872 (2) | 101 |
C6—H6B···N2 | 0.97 | 2.52 | 2.863 (3) | 101 |
C7—H7B···N2i | 0.97 | 2.52 | 2.858 (3) | 101 |
Symmetry code: (i) −x+1, y, −z+3/2. |